Ammonium Chloride → (3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

HRID 1677091ノート

反応式

HRID 1677091 の反応式
C(Cl)(=O)C(Cl)=O.[CH2:7]([O:14][C:15]([N:17]1[C@H:22]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=2)[CH2:21][O:20][CH2:19][C@@H:18]1[C@H:32]([OH:34])[CH3:33])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl-].[NH4+]>C(OCC)(=O)C.C(N(CC)CC)C.O1CCCC1.CS(C)=O>[CH2:7]([O:14][C:15]([N:17]1[C@H:22]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([F:30])=[C:25]([F:31])[CH:24]=2)[CH2:21][O:20][CH2:19][C@@H:18]1[C:32](=[O:34])[CH3:33])=[O:16])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

8

反応物 3

HCID 25517Ammonium ChlorideHCID 65578Oxalyl chlorideHCID 67373415(3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester

生成物 1

HCID 67372176(3R,5R)-3-acetyl-5-(3,4,5-trifluorophenyl)morpholine-4-carboxylic acid benzyl ester収率 91.4%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A tetrahydrofuran solution (15 mL) of dimethyl sulfoxide (0.22 mL) was cooled to −78° C., and oxalyl chloride (246 μL) was added dropwise into the resultant solution. The reaction solution was stirred for 5 minutes at the same temperature, and a tetrahydrofuran (5 mL) solution of (3R,5R)-3-((R)-1-hydroxyethyl)-5-(3,4,5-trifluorphenyl)morpholin-4-carboxylic acid benzyl ester (880 mg) was added dropwise. The resultant reaction solution was stirred for 1 hour at the same temperature, and triethylamine (1.54 mL) was added. The reaction solution was returned to room temperature, and stirring was continued for 1 hour. Ammonium chloride aqueous solution and ethyl acetate were added to the reaction solution, and the organic layer was partitioned, and the resultant was dried over anhydrous magnesium sulfate. The solvent was removed under a vacuum, and the resultant was purified by silica gel column chromatography (heptane/ethyl acetate), and the title compound (800 mg) was obtained. The physical property values are as follows.

後処理

  1. customThe resultant reaction solution
  2. additionwas added
  3. customwas returned to room temperature
  4. stirringstirring
  5. waitwas continued for 1 hour
  6. customthe organic layer was partitioned
  7. dry with materialthe resultant was dried over anhydrous magnesium sulfate
  8. customThe solvent was removed under a vacuum
  9. customthe resultant was purified by silica gel column chromatography (heptane/ethyl acetate)

出典と根拠

ORDレコード
ord-4bd99c254a3a48b6bebc5166a2f22a96
出典データセット
uspto-grants-2011_08
特許番号
US08008293B2

反応ノート

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